31 of the Best Things To Do in Chicago and the Suburbs in May 2023

Chicago’s greenery isn’t the only thing that flourishes in May. With the warmer weather, the city comes alive with outdoor — and indoor, too — marketplaces, eateries, performances, exhibits, community events and more. Whether you’re looking for something free to do on the weekend or want to grab tickets to Chicago’s hottest events — we’ve rounded up the best things to do in Chicago and the suburbs this month.

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All Month

Into the Woods


This Grammy-winning, Broadway darling visits Chicago’s James M. Nederlander Theatre for a limited run this spring, showing now through May 7. Fans know this story of interwoven fairytales to be about heart and truth as much as fantasy, but newcomers to the 40-plus year old show can expect a good laugh and, maybe, even shed a tear at one of Steven Sondheim’s most notable pieces. More details, photo sneak peeks and tickets can all be located on Broadway in Chicago.

24 W. Randolph St.

Andersonville Farmers Market


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Want to feel the pulse of the city again and get some local goodies, too? Enjoy one of the city’s first outdoor markets of the season, the Andersonville Farmers Market, now in its 14th year. Join vendors up on Catalpa Avenue between Clark Street and Ashland Avenue every Wednesday at 3-7pm for anything from local produce and honey to candles and tea, from May 10 until October. The vendors rotate per week, check out the Andersonville Farmers Market website for a full list of participating businesses and what else to expect when you shop.

The Arranged Flower: Ikebana and Flora in Japanese Prints

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The Art Institute‘s winding halls are home to a plethora or historic, impactful pieces of work. Among them for a limited time — and in celebration of Asian American Pacific Islander Heritage Month — is “The Arranged Flower: Ikebana and Flora in Japanese Prints” which detail “the artful display of flowers in Japanese culture known as ikebana (ike means “to arrange,” and bana or hana means “flowers”).” This medium of creativity has been honed for years and “remains a prominent and disciplined manifestation of a larger focus on nature in Japanese culture.” Grab your tickets on the Art Institute website, where details on this intricate exhibition can also be found.

111 S. Michigan Ave.

“Dark Side of the Moon” Experience at Adler Planetarium


The legendary rock album by Pink Floyd, “Dark Side of the Moon,” has inspired music lovers for decades. Now, experience it in a whole new light as Adler Planetarium celebrates the album’s 50th anniversary with an “epic” laser show. Get sucked into the magic “with lasers galore, and a 180-degree, 36-foot domed ceiling” making the show totally immersive — perfect for lovers of music and entertainment who like to get lost in the sound. The show will run until March 2024, but why wait to grab your tickets since the show kicks off in May — more information on the Adler Planetarium site.

1300 S. DuSable Lake Shore Dr.

The Real Housewives of Motown


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You know the sounds and legends of Motown, but do you know the stories of the first-ladies of Motown? Black Ensemble Theatre proudly presents “The Real Housewives of Motown,” their latest production that will take audiences on an “exciting musical journey as we discover what life was like for the women married to the stars.” Performances run on weekends, May 28 through July, but grab your tickets now before shows fill up! All details and tickets on the Black Ensemble Theatre website.

4450 N Clark St.

Dots Obsession at WNDR

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Global icon and artist Yayoi Kusama brings her extraordinary work to Chicago, specifically, the WNDR Museum. Experience “Dots Obsession” in all its vivid wonder, showing for a limited time starting May 12. Whether you’re a fan of the contemporary or are looking for something new to do, visit WNDR Museum online for more information and ticket sales.

1130 W. Monroe St.

May 3: Mom’s Night Out


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Looking for that perfect gift for mom, or want to treat yourself to a little something? Visit the Lakeview Roscoe Village area from 5-8pm for Mom’s Night Out — an evening of shopping local businesses, partaking in treats from pop-up vendors, playing games to win discounts and prizes and so much more. LRV is home to so many great stores, check out the Mom’s Night Out webpage for a full list of vendors and all other logistics.

May 4: Wine & Design: A Tasting Tour at THE MART


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When wine and art meet you end up with a little something like Wine & Design, a tasting tour held at THE MART — in partnership with Wine Spectator Magazine — from 6-8pm. “Enjoy tastings of wine from around the world with savory hors d’oeuvres while you tour the inspiring showrooms on the first floor.” For your opportunity to stroll through the iconic Chicago institution, visit THE MART online for registration and more.

222 Merchandise Mart Plaza

May 5-7: APIDA Arts Festival


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Asian, Pacific Island and Desi Americans (APIDA) Arts Festival is launching its exciting, inaugural year this month — to coincide with May being Asian American and Pacific Islander Heritage Month. Join the breadth of entertainment at various venues around Chicago — such as the Chicago Cultural Center and Goodman Theatre — as a number of artists showcase a wide range of creative work. The three-day showcase emphasizes “unifying APIDSAA artists in Chicago by … providing greater representation, equity and opportunity.” Visit APIDA Arts Festival for daily festival lineups and what else to expect; tickets can be purchased on the site as well.

May 6: The Lakefront Loop 5K


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In support of Navy Pier’s non-profit mission to “welcome all and provide dynamic arts and cultural experiences for our community,” they are hosting The Lakefront Loop — a 5K completely within the Pier’s grounds. The route will incorporate the Northwestern Medicine Wellness Way fitness trail, as well as the iconic North and South Docks. Want to know the perks? Each registration includes a t-shirt, a Centennial Ferris Wheel ticket and delicious donuts and beer waiting for you at the finish line. Register on the Navy Pier website.

800 E. Grand Ave.

May 6: The Batman in Concert


The latest iteration of the action-packed Batman saga comes to Auditorium Theatre for one night only, as a part of the touring series “DC in Concert.” Enjoy a screening of “The Batman” with the addition of a live production of the score. Feel the drama surge as Batman protects Gotham — parts of which were filmed in Chicago! Grab tickets at Auditorium Theatre online, more details can also be found there.

50 E. Ida B. Wells Dr.

May 6: Spring Sip ’N Stroll


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Shop, dine and explore through Evanton’s local-business friendly downtown. Support small businesses this May as you wander through stores; visit five or more to be entered into a raffle; and vote for your favorite floral window design featured at a number of participating locations. With over 20 businesses involved, you and the family are sure to find something you love or, at very least, get to know the businesses of your community. Head over to the Downtown Evanston website for all the details on how to shop and support this spring — registration is required for this free event.

May 6: Kentucky Derby Watch Party & Best Dressed Competition


Something about the classic traditions of the Kentucky Derby excite folks across the country every year. If you find yourself getting into the spirit of things, don your best Derby attire and head to Time Out Market Chicago for an afternoon of southern fun — don’t forget the Mint Julep! Before the race kicks off around 5:30pm, the most stylish guests will be dubbed the winner of the Best-Dressed Contest. Think it could be you? Check out all the details and find registration at Time Out Market Chicago.

916 W. Fullerton Ave.

May 6: A Peace of Pilsen Cinco de Mayo Bar Crawl and Community Celebration


The lengths people will go to celebrate Cinco de Mayo is beyond impressive, like the Peace of Pilsen Cinco de Mayo Bar Crawl and Community Celebration. It’s not just one party, but eight parties that are kicking off throughout the day with their own respective theme. From noon-6pm trolleys will bus participants from stop to stop, “partnering with some of the best bars in town to bring you an unforgettable celebration of Mexican culture and heritage.” They have quite the lineup in store, if you want to get in on the fun, head over to the registration page.

May 6-7: Art in Wilder Park


The Elmhurst Park District and Elmhurst Art Museum will host the 26th annual Art in Wilder Park, a free exhibition “featuring a variety of artisans selling one-of-a-kind jewelry, paintings, sculptures, ceramics, prints, and fiber arts, plus mouthwatering treats, family activities, and more ways to engage with the local community.” Special to this year’s program will be the unveiling of a newly-commissioned public art piece, Superheroes in Wilder Park — which will feature “life-sized superhero sculptures by area artists and youth groups.” Last year the series saw 8,000 visitors — help them surpass that number by visiting the Elmhurst Art Museum website to plan your trip.

175 S. Cottage Hill Ave., Elmhurst

May 7: Northshore Jazz & Classical Music Festival


In the summertime, nothing beats a family outing where everyone can find something to enjoy — if you venture to the Northshore Jazz & Classical Music Festival you just might find that and more! For the kids there are carnival rides, a cake walk, games and more. For the adults, enjoy a variety of food trucks against the backdrop of some stellar live jazz and classical music, and don’t forget about the silent auction to win tickets, prizes and more. Families can enjoy the free fun from noon-6pm, score the rest of the details on the Midwest Young Artists website — the sponsors of the event.

MYA Conservatory, 878 Lyster Rd., Highwood

May 9: MIBTV Virtual Event: National Fentanyl Awareness Day


Make It Better will be hosting yet another stimulating panel discussion — via live stream — this time with the focus on National Fentanyl Awareness Day. Parents and experts together will express the dangers of the fentanyl crisis in our country and how we can help navigate away from it. This pressing issue needs all the visibility it can get, visit the Better virtual events page for details on how to tune in to the broadcast and who to support.

May 11: Heroes Breakfast


For over 20 years, the American Red Cross of Greater Chicago “has honored individuals and groups for acts of immense bravery, dedication and service to the community” at their annual Heroes Breakfast. The Red Cross welcomes you to join them as they pay honor to our brave community members — from youth advocates to medical personnel and more. The event is 7:30-10am, held at the Chicago Hilton. Visit the Heroes Breakfast page for details and registration.

720 S. Michigan Ave.

May 8: A Book Stall Event: “Made in Chicago: Stories Behind 30 Great Hometown Bites” with Monica Eng and David Hammond


Journalists Monica Eng and David Hammond — an often contributor to Better — recently published “Made in Chicago: Stories Behind 30 Great Hometown Bites” cataloging the history and deliciousness of Chicago’s best food. Join them at the Highland Park Library as they discuss the book, sign autographs and enjoy samples with the audience — sponsored by The Book Stall. Food lovers and history lovers alike will take a lot from this one-time, free experience; find more details on The Book Stall website.

494 Laurel Ave., Highland Park

May 12-14: Chicago Mayfest

Courtesy of Star Events


Kick off the festival season in the city with the 26th annual Chicago Mayfest, held in Lincoln Park. Attendees can enjoy the sounds of some of Chicago’s best artists as they play across two stages, but it’s not just about the music, the Armitage Art Show will also be a central feature of the event. While parents enjoy the entertainment, tasty bites and delicious libations, kids will love the carnival area — making this the perfect summer stop for the whole family. Head over to Chicago Mayfest for what to know before you go.

May 12: Great Penguin Party at The Shedd


All the thrills of the roaring ‘20s — and none of the prohibition — is alive and well at The Shedd Aquarium thanks to The Great Penguin Party. Grab cocktails and hors d’oeuvres, swing to the live orchestra and peruse the animals that call The Shedd home — and be sure to check out the penguins, who are already sporting their tuxedos. Tickets can be purchased and event details can be found at The Shedd.

1200 S. DuSable Lake Shore Dr.

May 13: Spring Fun Fest


Parkway Bank Park is calling all families to the annual Spring Fun Fest, an afternoon outdoors where kids can enjoy a range of exciting activities. Running from 1-5pm, this free event offers bounce houses, a petting zoo, balloon sculptors, face painting and live entertainment from Jeanie B. and the Jelly Beans. If you’re in the market for some summer fun that’s easy on the wallet, Spring Fun Fest is a good place to be.

5501 Park Pl., Rosemont

May 13-14: Midwest Bonsai Society Spring Show & Sale


Beloved by many, the Midwest Bonsai Society Spring Show & Sale returns to the Chicago Botanic Garden this May. From 9am-5pm, marvel at the flowering bonsai, bonsai on rocks, bonsai trees in various stages of development and suiseki — which is the Japanese art of stones. There will be hundreds of bonsai specimens on display and for sale, as well as free demonstrations, lectures and workshops for all levels of bonsai enthusiasts. Register on the Chicago Botanic Garden website.

1000 Lake Cook Rd., Glencoe

May 17: Spring Floral Design Workshop with Leelee’s Garden


Have you always wanted to have that perfect centerpiece? Or just the right bouquet to brighten a room? Well this hands-on workshop will walk you through the steps to creating your very own with the guidance of Leelee of Leelee’s Garden. The two-hour event will be hosted at the InterContinental Chicago, and could be the perfect gift for mom. Let your creativity blossom, view more details and save your spot on the Spring Floral Design Workshop webpage.

505 Michigan Ave.

May 18: Evanston Arts & Craft Beverage Crawl


The highlight to this art crawl is the importance of locally-owned businesses, such as the “delicious Evanston-made boozy beverages and fun food pairings” that guests can enjoy during this three hour fest. While there, see inspiring local artists’ work, some live entertainment and get a a goody bag to top it all off. There are countless vendors and a whole lot of fun in store, check out the Evanston Arts & Craft Beverage Crawl page to find all the details and grab tickets.

The Main-Dempster Mile, 900 Chicago Ave., Evanston, Illinois

May 20-21: Dance Divas 2023 “A Night at the Movies”


If an evening of “high heels and high camp” sounds up your alley then you ought to check out Dance Divas 2023 — a program that unites artists from the Chicago professional dance community. This year’s theme is “A Night at the Movies,” and will feature performers paying homage to the stars of the silver screen. All proceeds will benefit The Dancers’ Fund, which provides short-term financial assistance to Chicago dance industry professionals for preventative health care and critical medical needs. Help keep Chicago’s creative scene alive by seeing the show and supporting the artists — tickets can be purchased on the Dance Divas site.

4713 N. Broadway

May 20-21: Northbrook Art in the Park


At this summer’s Northbrook Art in the Park, attendees not only get to explore over 85 origianl artists, but they get to be one, too! When not viewing art, listening to live music or enjoying the delicious treats at the fest — like Italian ice, empanadas, churros and more — take part in a live painting class or stop into the Kid’s Creation Station for games and activities. Bring the family and enjoy a summer afternoon in the suburbs — find a lineup of events and vendors at Northbrook Art in the Park.

May 20-21: Skokie Festival of Cultures


To honor all the cultures represented in Chicagoland — known for being a melting pot — the Skokie Festival of Cultures returns for another triumphant summer. Held at Oakton Park in Skokie, the festival will feature music and dance on stage; food and beverage vendors; interactive cultural booths; children’s game and activity area; the festival’s famous flag display and much more. What a great opportunity to experience something you may not otherwise — check out the Skokie Festival of Cultures for more information.

4701 Oakton St., Skokie

May 22: The Trail of Socrates


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Pedants of philosophy gather round as “nationally renowned attorneys and judges take on ancient Greece’s most famous court case: The People vs. Socrates.” Presented by The National Hellenic Museum and held at the Harris Theatre — just outside Millennium Park — the show will unravel the age-old debate for all of Chicago to see; starring John Kapelos (The Shape of Water, The Breakfast Club) as Socrates himself. Tickets are on sale now, visit The Trail of Socrates online for more.

May 24: Summer Screenings Program


Cinema/Chicago — known for shining a light on films that may not have a wide reception in America — is once again hosting their Summer Screenings Program from May 24-September 30. In conjunction with the City of Chicago’s Department of Cultural Affairs and Special Events, these free weekly screenings will put a spotlight on, and examine, various countries’ cinema. Stay tuned for their full lineup of films, to be posted on the Cinema/Chicago website — tickets can be found there, too.

May 26-28: Mole de Mayo


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If you’ve got a taste for Mexican food, then you’re no stranger to the delicious sauce used across the cuisine: mole. Each person who makes this traditional sauce has their own flare, which is how the Mole de Mayo was born. Enjoy sampling food from over 20 “popular festival food vendors, each bringing their own savory, sweet or spicy version of mole.” After you’ve gotten your fill, vote for who will be the 2023 People’s Choice and Best Mole winner. A full list of details, locations and everything you need to know can be found on the Mole de Mayo website.

May 27: The Forge Blues & Brews Festival 


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Head out to Lemont for The Forge Blues & Brews Fest, where the admission is only $5 for the first 1,000 registrants. Once inside, soak up a day full of live blues music from renowned artists, including Joanna Connor. To accompany that music will be 15 featured Illinois breweries, each ready for sampling. Check out the Blues & Brews Festival to register and find out what else there is to get excited about.

1001 Main St., Lemont

May 27-28: Belmont-Sheffield Music Fest


The Belmont-Sheffield Music Fest is ringing in its 38th year this summer, and with all that success under their belt, we doubt they will disappoint. Join them in Lakeview for can’t-miss local tribute bands, great eats, strong libations and, best of all, see your community members entertain with music acts, DJing and other performances. The summer brings us all out into the city, so enjoy yourself while you’re at it! Got questions? Peruse the Belmont-Sheffield Music Fest website for more.

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Margaret Smith is a Chicago-based writer and editor with a passion for socio-political storytelling about their community. They are a graduate of Columbia College Chicago.

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